4-Toluenesulfonyl chloride → 2-Methoxy-4-(2-{[(4-methylphenyl)sulfonyl]oxy}ethyl)phenyl acetate

HRID 1805929

Reaktionsgleichung

Reaktionsgleichung von HRID 1805929
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:12]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][OH:24])=[CH:18][C:17]=1[O:25][CH3:26])(=[O:14])[CH3:13]>N1C=CC=CC=1.O>[C:12]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][O:24][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])=[CH:18][C:17]=1[O:25][CH3:26])(=[O:14])[CH3:13]

Komponenten

5

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 673766674-(2-Hydroxyethyl)-2-methoxyphenyl acetate

Produkt 1

HCID 866573972-Methoxy-4-(2-{[(4-methylphenyl)sulfonyl]oxy}ethyl)phenyl acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

p-Toluenesulfonyl chloride (2.14 mL, 11.2 mmol) was added to a stirred solution of 4-(2-hydroxyethyl)-2-methoxyphenyl acetate (1.18 g, 5.61 mmol) in dry pyridine (20 mL) at 0° C. under N2. The reaction was stored at 4° C. for 3 days. The reaction was diluted with water (50 mL) and extracted with EtOAc (3×50 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to afford 2-methoxy-4-(2-{[(4-methylphenyl)sulfonyl]oxy}ethyl)phenyl acetate, as an oil. Product was a 6:4 mixture of desired product and starting material but carried forward regardless. LCMS calc.=387.1; found=386.8 (M+Na)+.

Aufarbeitung

  1. extractionextracted with EtOAc (3×50 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cd150b8f687f43d69e083cf44bdacb20
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354454B2

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